Great piece. I completely agree that there is no one universal answer to the question of which is better between being an employee or self-employed. The answer changes not only from one person to the next, but also over time for the same person.

As for your list of drawbacks, I have a few suggestions to mitigate them:

• “You have no one else to rely on” — you can hire people, either as employees or as independent contractors
• “You do not have a manager setting tasks or deadlines, so all deadlines are self-imposed, which can be difficult for some to manage and stick to”— you can hire a good business coach; that coach will not have authority to set consequences for not meeting deadlines, but if you don’t meet your own deadlines despite the coach’s support, your clients will take care of the consequences :).
• “Time management becomes extremely important, which is hard for many” — I recommend using the simplest tools that will get the job done; I use Google Calendar and Google tasks
• “No company insurance or other benefits” — which makes it important that you buy your own coverages; depending on your specific circumstances, that may include general liability, professional liability, malpractice, workers comp (if you have employees), health, etc.
• “No sick time, paid vacation time, or maternity leave” — on the contrary, you get all the sick time, vacation, and leave you want; you just have to price those into your rates.
• “Less stability in terms of income” — which is why you always need to be marketing, especially when you’re busy with current work; in addition, you need a larger emergency fund than if you have a stable salary.
• “You will find yourself working far more than 40 hours most weeks” — too true; the only way to avoid this is to set your rates high enough and your expenses low enough that you’re happy with revenues that you can produce working fewer hours.
• “You do not have coworkers and it can be sometimes lonely and isolating” — this depends on how you work with clients; personally, I work 3 or more days a week at a client location, so this isn’t a problem; when this wasn’t so, I’d work at a local coffee shop and got to know the staff and a lot of the regulars; it also helps to find a good networking group.
• “You are probably not an expert in every single thing a business needs: processes, sales, closing sales, marketing, website building and maintenance, creative stuff, contracts, organization, admin work, etc.” — Amen and amen again to that; this is why you should hire a good accounting/payroll company, a good employment attorney and HR consultant (if you have employees), etc.
• “Higher potential for burnout/overworking” — this is similar to the working more than 40 hours most weeks; setting your rates right helps with this; taking a good number of vacations and staycations also helps (and if you feel that you can afford to do so, set your rates higher).
• “Doing your taxes is harder” — did I mention hiring a good accountant?

Hiring a good business coach and/or getting involved in a strong networking group are good ideas if you’re targeting a 6-figure income (or higher).